Abstract (English)

Through esterification, benzylation, oxidation with m-CPBA and subsequent rearrangement reaction, 3-hydroxypicolinic acid could be converted to the key intermediate, 3-benzyloxy-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid methyl ester (1), which could be transformed into new 3-piperidinol chiral building blocks.
A new facile method for the synthesis of new vitamin C analogue (2) was developed. ...

Abstract (English)

Through esterification, benzylation, oxidation with m-CPBA and subsequent rearrangement reaction, 3-hydroxypicolinic acid could be converted to the key intermediate, 3-benzyloxy-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid methyl ester (1), which could be transformed into new 3-piperidinol chiral building blocks.A new facile method for the synthesis of new vitamin C analogue (2) was developed. After the regioselective protection for 5,6-diol from vitamin C, followed by the selective acetylation in 2-position, and subsequent triflation for the left 3-hydroxy group, a key intermediate 3-triflate (3) was obtained in good yield, which could couple with different boronic acids to afford the corresponding 3-deoxy-3-Aryl vitamin C derivatives. After further deprotection, the designed compound 3-deoxy-3-(2-hydroxyphenyl)-L-ascorbic acid (4) was obtained in good yield.